Downtown Winchester, Virginia









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Shop Downtown Discount Card

Discounts For Customers - Support Local Businesses - Fight Cancer

When you purchase a Shop Downtown Discount Card for $10, you help support your neighbors, local economy and the American Cancer Society's mission to save lives, celebrate lives and lead the fight for a world without cancer. You also ensure great savings on a variety of products and services every time you patronize a participating member. It's a win/win situation.

Shop Downtown will contribute 100% of the sale price of each discount card sold through December 31, 2021, to American Cancer Society Relay For Life. The American Cancer Society does not endorse any product or service.









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Things to do in Winchester, Virginia

Main Street of old Downtown Winchester speaks to once what was and what could be once again. As Winchester the community gathers, it leaves a pocket of opportunity for small business owners to come in and set up shop.Take a few minutes to explore what each downtown has to offer by viewing our directory below.

Downtown Winchester brings smiles by way of doughnuts and pastries made fresh daily for your enjoyment. Everyone has their favorite of course but having a variety of bakeries is what makes downtown so special. Fritters, scones and pies oh my!

Downtown Winchester has that special dining venue and you are sure to find something to please with numerous meals served to satisfy each palette. A wide variety of restaurants and delis are available to choose from with a nice selection of entrees and especially desserts.

Downtown Winchester thanks the collection of small business owners who devote their time and energy to make shopping downtown a great experience. Inventory offered downtown is shopped by the merchant buyer to bring the best products to your neighborhood.

Downtown Winchester offers on-the-go dining when you visit your favorite food truck. Pick up some corn tortilla tacos with freshly made pico with a fresh squeeze of lemon to give your day a boost. Food trucks can offer a wide variety of niche ethnic blends.

Why do you love downtown?

Kathy Burchett
I've never been and I would like to visit the downtown area, during my visit. During our last visit, we were not aware of a downtown area. Thank You!!!

Robert Drennan
Planning a trip and want to visit after reading all the reviews

Angela Shields
I will be visiting Ashland for the first time this coming weekend! I have heard from numerous people what a great town it is and how much I will like it. Very excited to check it out and do some shopping!

Channal Styers
Will be my first visit taking Easter train ride on Saturday to Watertown super excited see what in this great town!

Deborah
Jacksonville is utterly charming! I love browsing Terra Firma and Pickety Place, eating delicious Umi Sushi, and sitting under the amazing wisteria in the Bella Union garden. I always go to the library in that sweet little building, where Lauren the librarian knows me by name (and recommends good books). The Good Bean people are awfully nice, and even the clerks at Umpqua Bank are especially kind and friendly. Best little downtown ever!

Restaurants in Winchester, Virginia


A Matter Of Taste

175 Horizon Drive
Downtown Winchester



Apple Blossom Country Market

1184 Millwood Pike G
Downtown Winchester



Allen Properties

1042 Berryville Avenue
Downtown Winchester



Bedrock Group

168 North Loudoun St
Downtown Winchester




Downtown Winchester Hotels

Finding the best hotel in Downtown Winchester can make or break the experience of your entire trip. Take a few minutes to explore what each hotel has to offer by viewing our directory below. Here are some tips to consider:

Other sources of noise can be opening and closing trash dumpsters and also during collection by garbage trucks. Another great question is if they have any renovation plans, or underway that could affect your ability to relax. Pack earplugs and eyeshades!

Always tip staff when you feel the service was great and don't forget the housekeeping staff which you may never see. You should tip every day if you are staying multiple days as the staff may rotate out and miss the bounty at the end.

Policies vary on the availability of pet friendly rooms to it is wise to be open, honest and upfront during the booking process. You may find yourself kicked out or even paying a large deposit if you are not in a pet-friendly hotel and bring one anyway. New ADA laws are fuzzy though as service animals are not required to be documented and proprietors are legally not allowed to ask if the animal is a pet vs. a service animal.